Chemotaxonomy is a tool to assist in the accurate

positioning of a plant within a system; give illustrations

of how it may be useful in the quest for new medicines
or food.
Introduction
The science of taxonomy in plants is aimed at delivering a system for
classifying all plant groups in a way which represents best the similarities
and differences. The concept of classification of plant based on chemical
character is not new as Greshoff in 1909 suggested that chemical
characters should be included in classification of taxa (Hegnauer, 1967).
Chemotaxonomy was developed vastly through the 20th century although
it has advanced taxonomy through the study and identification of the
similarities and differences of chemical substances in plants, which has
thus enabled taxonomists to more accurately position plants. There are
many different definitions for chemotaxonomy but an author (Hegnauer,
1967) described it in relation to plants as a scientific investigation of the
potentialities of chemical characters for the study of problems of plant
taxonomy and plant phylogeny. Chemotaxonomy not only deals with the
investigation of plants metabolites and other products such as
carbohydrates and amino acids, it is also concerned with evolutionary
change, chemical convergence and divergence in the plant. Biosynthetic
pathways are also used to position plants. Analytical techniques such as
chromatography and electrophoresis allow analysis of plants to be made
quickly using minimal plant material and can detect small traces of
chemicals. Further analysis can be carried out to give fingerprints and
detailed compositions of samples using nuclear magnetic resonance
spectroscopy (NMR) and mass spectrometry (MS) (Walton and Brown,
1999). Continued investigation has permitted the development of
extensive data for classifying the position of plants, which can then be
applied when looking for taxa with potential for medicinal compounds and
foods.

Discussion
Classification of plants without the investigation of chemical constituents
(chemotaxonomy) is assessed through examination of the morphology of
the taxa that is under scrutiny. This would be inadequate in defining taxa
accurately and therefore the study of chemotaxonomic classification has
added considerable significance in positioning taxa within the appropriate

system (Bhargava, Patel and Desai, 2013). Plants of the same family
commonly synthesise similar compounds as they often contain analogous
enzymes, producing similar biosynthetic pathways. It is also possible for
the same metabolites can be the product of two quite different pathways.
Chemotaxonomic studies include the investigation of the pattern of
compound occurring in the plant and preferentially various explants such
as the bark, wood, leaves, root, fruits and seeds. Holistic investigations
are necessary in order to achieve substantial evidence for the taxa being
studied, which should include testing on an acceptable number of
specimens of the plants in order to classify the plants as a whole.
Organic compounds within plants are recognised as primary metabolites,
secondary metabolites and semantides. Primary metabolites such as
acotinic acid and citric acid are present in the Krebs cycle and therefore
may not be beneficial in systematically positioning a plant; however the
varying quantities of these metabolites in different plants may be of use
(Stace, 1989). Secondary metabolites have limited prevalence which
makes them much more valuable in positioning plants. They have nonessential functions which are less fundamentally widespread in plants as
with primary metabolites used for growth, reproduction and
photosynthesis (Stace, 1989). Secondary metabolite functions are, as well
as regulating primary metabolic pathways, often evolved to aid plants to
survive and thrive in their environment. Examples are pigments, tastes
and scents which can attract pollinators or repel herbivores, insects and
microorganisms, while others may act as poisons. These secondary
metabolites as mentioned may be specific to a genus and therefore can
act as reliable taxonomy markers. This can be of aid when screening taxa
for the possibility of a particular secondary metabolite. The biosynthesis of
secondary metabolites has a tendency to be in specialised cells and with
not being used in metabolic functions are in smaller quantities to that of
primary metabolites (Balandrin et al., 1985). Higher plants produce many
organic compounds with the potential to be valuable medicinally and
therefore commercially also, however it is still the case that many have
still not been analysed for their chemically characterised (Balandrin et al.,
1985). Chemotaxonomy is continuing to expand the portfolio of
biologically active compounds by positioning plants within appropriate
systems.
The use of plants in pharmaceuticals is extensive with many medicinal
products utilising chemicals naturally produced by plants or semisynthetic modified plant chemicals. They may also be used in the
development of insecticides or genetically modified foods that are less
susceptible to being attacked by herbivores and insects. Some common
types of secondary metabolites are alkaloids, flavonoids, terpenoids,

cyanogenic glycosides, glucosinolates and phenolic compounds (Stace,

1989). By exploiting chemotaxonomy, there is still scope for development
of new medicines and food from plants.
Extensive use of chemotaxonomy requires a good understanding of the
bio-chemistry and distribution of plants. Phytochemicals naturally
fluctuate in their distribution within a plant. The quantity and constitution
of composites such as alkaloids, terpinoids and flavonoids and the many
subclasses are controlled by the plants maturity, where the culture is
taken from (e.g. leaves, roots, stem, and flower), the location it grows and
its environment. Variation as a result of local ecology may be the result of
the phenotypic plasticity as a result of being exposed to heterogeneity in
the surrounding environment and understanding this can be vital for
predicting changes in distribution, chemical composition, and crop yields
as a result of climate change (Gratani, 2014), and therefore useful for
future quests for new food and medicines from plants. Genetic variation in
local populations is called polymorphism and is where variations lead to
new races by migration and natural selection (Hegnauer, 1986). Plant
species with extensive geographical range can have great variations in
physiology, morphology and phenology, so will often produce closely
related however different secondary metabolites. An example where this
has proved useful is with taxol (paclitaxel) which is an effective anticancer
drug. It is a taxane alkaloid (diterpinoid) extracted from the inner bark of
the pacific yew tree, Taxus brevifolia, which are rare. A problem is that
only low concentrations are stored in the bark and there are extremely
high extraction costs. The extraction process is also destructive and leads
to death of the yew trees, which with high demand means isolating it from
this source is unsustainable and requires alternatives to obtain the drug
especially for conservation of the species. One source where taxol can
also be semi synthetically produced is by extracting 10-deacetylbaccatin
(10-DAB) found in the needles of European yew trees, Taxus baccata.
There are also cost extraction issues with this process and supplies can be
affected by climatic changes, environmental damage and harvesting
problems. New advancement in technologies means that there are new
promising methods to sustainably make the precursor material such as
plant cell-based fermentation at industrial levels (MacDonald, 2013).
Without chemical taxonomic data carried out on the Taxus species it would
not have been possible to sustain production of paclitaxel and this also led
to the discovery of the a similar compound made from the Taxus baccata
called docetaxel, which is also in clinical use as an effective anticancer
drug.
Going back to polymorphism, an example of this is cyanogenesis that is
the release of hydrogen cyanide (HCN) after cell damage. Usually

cyanogenesis depends upon the presence of cyanogenic glycosides and

corresponding enzymatic hydrolysis in a given tissue. Plant families which
contain cyanogenic glycosides are Fabaceae, Rosaceae, Linaceae,
Different L-amino acids like phenylalanine, tyrosine, valine, leucine, and
isoleucine are precursors for the biosynthesis of cyanogenic glycosides,
but they are restricted to particular family e.g. leucine to leguminosae and
sapindaceae. The presence or lack or presence of cyanogenetic glycoside
can therefore be used as a chemotaxonomic marker (Vetter, 2000).
Alkaloids are basic compounds, usually containing heterocyclic nitrogen
with exceptions such as ephedrine and generally complex structures. They
are naturally occurring so are produced from plants. There are various
classifications of alkaloids; true alkaloids such as atropine have a nitrogencontaining heterocylic ring derived from amino acids; protoalkaloids
derived from amino acids but lacking nitrogen in a heterocyclic ring such
as ephedrine; pseudo alkaloids not derived from amino acids. Most of
them derived from- terpenes, sterols, nicotinic acid or purines. There are
also false alkaloids which give a false positive test when subjected to
alkaloid reagents Alkaloids come mostly from higher plants particularly in
the dicotyledons, and are in abundance in the angiosperms. Alkaloids, due
to their basic nature, generally exist as a salt of organic acid such as
oxalic acid. Some alkaloids occur free in nature while a few occur as
glycosides such as solanine in solanum (Hegnauer, 1963). It has been
found that amino acids phenylalanine, ornithine, tryptophan, lysine,
histidine, anthracitic acid are primary precursors of alkaloids in plants.
Each of this amino acid can be regarded as starting point for synthesis of
one or more types of alkaloids and therefore alkaloids can be placed into
families corresponding to those six amino acids (Wink, 1999). Some
alkaloids only occur in certain plants e.g. Morphine from P. somniferum or
strychnine is restricted to the strychnos class. So we can see there are
instances and specifics which can be used in order to classify alkaloids
using chemotaxonomy.
Hegnauer(1967) wrote of the interest in the steroidal alkaloids of Buxus
sempcrvirens and how other species of Buxus and genera of the Buxaceae
were studied for similar alkaloid substances. Similar compounds were
detected in the genera Pachysandra and Sarcococca despite having
differing morphology to the original plant where the first discovery was
made.
Many drugs discovered many years ago still used today are from natural
sources, such as quinine - Cinchona bark, morphine and codeine - latex of
the Papaver somniferum, digoxin - Digitalis leaves. Newer drugs have also
been discovered Anticancer drugs such as previously mentioned taxanes,

vinblastine and vincristine from Madagascar periwinkle - Catharanthus

roseus and etoposide from American mayapple Podophyllum peltatum.
The resin podophyllin obtained from the root of the Podophyllum peltatum
is toxic and is used clinically to remove warts. The major component of
the resin is podophyllotoxin which inhibits cell division and while the resin
is toxic, using the chemical characteristics and modifying them enabled
the production of the semi-synthetic glucoside, etoposide (Phillipson,
2001).
Despite these innovations in phytochemistry many pharmaceutical
companies have invested heavily in synthetic drugs more so than plant
derived drugs recently (Walton and Brown, 1999). These produced many
successful new medicines such as bisoprolol, ramipril, formeterol and
lorazepam, all used for different treatments from hypertension to asthma.
However often nature is able to produce unique chemical structures which
may likely be undiscovered without chemotaxonomic research.
The secondary metabolite group terpinoids encompasses a vast range of
terpenes and indicates that they are all based on a common chemical
structure, isoprene, and have the formula C5H8.

The series includes essential oils such as the volatile substances

monoterpenes and sesquiterpenes, less volatile diterpenes, non-volatile
triterpenoids and sterols and carotenoid pigments.
Artemisinin is a sesquiterpene endoperoxide that has been isolated from
the Chinese antimalarial herb Artemisia annua. It has been shown to be
an effective antimalarial against resistant strains of Plasmodium
falciparum the cause of human malignant cerebral malaria. Semisynthetic derivatives including artemether have enhanced
pharmacokinetics and are also used clinically. Further studies of a range of
plants used in traditional medicine for the treatment of malaria has led to
the isolation of a series of other compounds with activity against P.
falciparum including isoquinoline and indole alkaloids, flavonoids, mono-,
di- and sesquiterpenoids (Phillipson, 2001).
We can see discovery of active compounds from plants which are then
characterised and classified may lead to new medicinal compounds or
other useful products or they may just offer a starting compound which
can be modified. Modifying existing structures can be less financially risky

for drug companies who may simply look to optimise the activity of a
compound already known (Walton and Brown, 1999).

Conclusion
Plants are essentially chemical factories Walton and Brown wrote (1999)
which naturally synthesise extremely diverse complex structures tailored
for their needs. Chemotaxonomy has already proved to be of great
benefits in the discovery of drugs. Even when phytochemicals have been
used for many years, with the new analysis methods at disposal we have
been able to identify and isolate active chemicals that we want and refine
them from unwanted chemicals which may be present. New complex
secondary metabolites are being revealed and categorised all the time
and so the understanding of biosynthesis and chemotaxonomy of plants is
far from complete even for known plants. It is understood that when
chemicals are detected within a sample that any not expected should be
investigated further as even very small quantities may be the result of
contamination or possibly indicative of the occurrence polymorphism due
to ecological stresses from where it was sourced. With the changes in
climate that are well documented and predicted to continue there may
well be manifestations in plants through changes in biochemical as a
result. An estimated only 20-30% of the worlds plants have undergone
chemotaxonomy (Walton and Brown, 1999) and continued phytochemical
and pharmacological studies will no doubt provide new sources for
medicines and foods. With the developments in technology it is growing
more possible to use chemical data from plants and investigate if the
phytochemicals of interest in them can be made in a more sustainable
manner without the need to cultivate and harvest them from plant
sources. The use of plant cell cultures is one aspect which is benefiting
both chemical characterisation and industrial production. But with
certainty it can be said that any quests for new medicines or foods from
plants will be more successful with a chemotaxonomy approach.

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